European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 22

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.065

ISI Journal Citation Reports © Ranking: 2014: 13/57 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry


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  1. Full Papers

    1. Fluorinated Sulfoxides

      Circular Dichroism and TDDFT Investigation of Chiral Fluorinated Aryl Benzyl Sulfoxides

      Roberto Berardozzi, Ciro A. Guido, Maria Annunziata M. Capozzi, Cosimo Cardellicchio, Lorenzo Di Bari and Gennaro Pescitelli

      Article first published online: 28 JUL 2015 | DOI: 10.1002/ejoc.201500648

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      A series of ten chiral aryl benzyl sulfoxides with perfluorinated aromatic rings has been investigated by means of electronic circular dichroism and time-dependent DFT calculations. The perfluorination has a large impact on the molecular orbitals and electronic transitions. Range-separated functionals perform much better than global hybrids in the prediction of the ECD spectra.

    2. Porphyrinoids

      Insights into the Synthesis and the Solution Behavior of meso-Aryloxy- and Alkoxy-Substituted Porphyrins

      Kirill P. Birin, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Alla G. Bessmertnykh-Lemeune and Roger Guilard

      Article first published online: 28 JUL 2015 | DOI: 10.1002/ejoc.201500628

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      Synthetic approaches to meso-RO-porphyrins were investigated. Mono- and di-RO-substituted porphyrins were synthesized from 5,15-dibromoporphyrins by using an SNAr reaction. Furthermore, unsymmetrical porphyrinyl alkyl ethers were prepared from NiII 5-bromo-15-RO-porphyrin by using Pd-catalyzed coupling reactions. Concentration-dependent aggregation of ZnII meso-RO-porphyrins was studied by NMR spectroscopy.

    3. Alkyne-Azide Cycloaddition

      Metal-Free Intramolecular Alkyne-Azide Cycloaddition To Construct the Pyraz­olo[4,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine Ring System

      Eglė Arbačiauskienė, Vaida Laukaitytė, Wolfgang Holzer and Algirdas Šačkus

      Article first published online: 28 JUL 2015 | DOI: 10.1002/ejoc.201500541

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      A new pyrazolo[4,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine ring system was synthesized by employing a metal-free, intramolecular alkyne-azide cycloaddition reaction that uses readily available starting materials.

  2. Short Communications

    1. Iron-Catalyzed Aromatization

      Fe(OTf)3-Catalyzed Aromatization of Substituted 3-Methyleneindoline and Benzo­furan Derivatives: A Selective Route to C-3-Alkylated Indoles and Benzofurans

      Sandip Kundal, Swapnadeep Jalal, Kartick Paul and Umasish Jana

      Article first published online: 27 JUL 2015 | DOI: 10.1002/ejoc.201500540

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      A simple selective synthesis of 3-substituted indoles and benzofurans by isomerization of 3-methyleneindoline and benzofuran derivatives with Fe(OTf)3 was developed. The substrates were obtained by the domino Heck–Suzuki coupling of 2-bromo-N-propargylamide or 2-bromopropargyl ether. The method features high yields, mild reaction conditions, wide functional group tolerance, and an environmentally friendly catalyst.

  3. Full Papers

    1. Carbazole Synthesis

      Gram Scale Total Synthesis of 2-Hydroxy-3-methylcarbazole, Pyrano[3,2-a]carbazole and Prenylcarbazole Alkaloids

      Jianxin Dai, Dengke Ma, Chunling Fu and Shengming Ma

      Article first published online: 27 JUL 2015 | DOI: 10.1002/ejoc.201500783

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      Carbazole alkaloid natural products including 2-hydroxy-3-methylcarbazole, girinimbine, murrayacine, mukoenine-A, and heptaphylline have been produced on gram scale. Girinimbine and murrayacine were synthesized using PhB(OH)2-mediated intermolecular cyclization with 3-methylbut-2-enal whereas mukoenine-A and heptaphylline were best accessed using a Pd-catalyzed allylation/Claisen rearrangement.

  4. Corrections

    1. You have free access to this content
      Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclodo­decindione Type

      Johannes Tauber, Kristina Rudolph, Markus Rohr, Gerhard Erkel and Till Opatz

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500930

      This article corrects:

      Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclododecindione Type

      Vol. 2015, Issue 16, 3587–3608, Article first published online: 21 APR 2015

  5. Full Papers

    1. Luminescent Pigments

      First Demonstration of the Applicability of the Latent Pigment Approach to Plastic Luminescent Solar Concentrators

      Sara Mattiello, Alessandro Sanzone, Paolo Brazzo, Mauro Sassi and Luca Beverina

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500554

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      First demonstration of the applicability of the latent pigment approach to plastic luminescent solar concentrators The latent pigment approach enables the straightforward preparation of stable single-layer plastic luminescent solar concentrators based on the otherwise non-emissive and insoluble quinacridone and perylenediimide pigments.

    2. Dye-Sensitized Solar Cells

      Fluoren-9-ylidene-Based Dyes for Dye-Sensitized Solar Cells

      Alexis Tigreros, Danisha M. Rivera-Nazario, Alejandro Ortiz, Nazario Martin, Braulio Insuasty and Luis A. Echegoyen

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500602

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      Three dyes with hindered fluoren-9-ylidene hydrophobic groups as antennas are synthesized, and their electrochemical, photophysical, and photovoltaic properties are evaluated. As the starburst shape of the dyes increases, the open-cell voltage (VOC) increases from 0.79 to 0.83 V, which leads to an increase of 18 % in the power-conversion efficiency (PCE).

    3. Decarbonylative Cross-Coupling

      Nickel-Catalyzed Decarbonylative Cou­pling of Aryl Esters and Arylboronic Acids

      Nicole A. LaBerge and Jennifer A. Love

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500630

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      Functionalized bis(hetero)aryl motifs are easily accessed from heteroaryl esters and boronic acids by using decarbonylative coupling. The Suzuki–Miyaura-type cross-coupling is catalyzed by an affordable low-toxic catalyst system composed of Ni(cod)2 and PCy3. This methodology presents an attractive alternative to the use of palladium catalysts currently used in industry to acquire bis(hetero)aryls.

    4. Ribonucleotides

      mRNA Cap Modification through Carb­amate Chemistry: Synthesis of Amino- and Carboxy-Functionalised Cap Analogues Suitable for Labelling and Bioconjugation

      Marcin Warminski, Zofia Warminska, Joanna Kowalska and Jacek Jemielity

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500672

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      A series of amino- and carboxy-functionalised dinucleotide 5′ cap analogues have been synthesised by use of carbamate chemistry. The compounds are suitable for labelling with biotin or fluorescent tags by employment of an in situ NHS activation strategy,

  6. Short Communications

    1. Water-Soluble Phosphanes

      Tetrasulfonated 1,2-Bis(diphenylphosphanyl)ethane as a Building Block for the Synthesis of Disulfonated Alkyldiphenylphosphanes

      Julien Denis, Michel Ferreira, Hervé Bricout, Cécile Machut, Sébastien Tilloy and Eric Monflier

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500772

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      A new methodology for the synthesis of disulfonated alkyldiphenylphosphanes bearing an oleum-sensitive group has been developed. Alkylation of 1,2-bis(diphenylphosphanyl)ethane (DPPETS) followed by cleavage gives the desired disulfonated alkyldiphenylphosphane products.

  7. Full Papers

    1. Iron Catalysis

      Synthesis of (R)-BINOL-Derived (Cyclopentadienone)iron Complexes and Their Application in the Catalytic Asymmetric Hydrogenation of Ketones

      Piotr Gajewski, Marc Renom-Carrasco, Sofia Vailati Facchini, Luca Pignataro, Laurent Lefort, Johannes G. de Vries, Raffaella Ferraccioli, Umberto Piarulli and Cesare Gennari

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500796

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      A family of chiral (cyclopentadienone)iron complexes with an (R)-BINOL-derived backbone is described. The complexes differ in the substituents at the 3,3′-positions of the binaphthyl residue (H, OH, OR, OCOR, or OSO2R) or at the 2,5-positions of the cyclopentadienone ring (trimethylsilyl, or Ph) and provide up to 77 % ee in the asymmetric hydrogenation of ketones.

    2. Near-Infrared Probes

      Near-Infrared Fluorescent 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene Probes for One- and Two-Photon Fluorescence Bio­imaging

      Bosung Kim, Xiling Yue, Binglin Sui, Xinfu Zhang, Yi Xiao, Mykhailo V. Bondar, Junko Sawada, Masanobu Komatsu and Kevin D. Belfield

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500664

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      Two new BODIPY-based near-IR emitting fluorescent dyes were investigated that have a high lysosomal selectivity and – when incorporated in silica nanoparticles surface-functionalized with the RGD peptide – afford thick-tissue vascular imaging.

  8. Short Communications

    1. P-Chiral Cage Phosphines

      Diastereoselective [4+2] Cycloaddition Reaction of 1-Neomenthyl-1,2-diphosphole: Facile Synthesis of P-Chiral Cage Phosphines

      Almaz Zagidullin, Vasili Miluykov, Fedor Polyancev, Shamil Latypov, Oleg Sinyashin, Peter Lönnecke and Evamarie Hey-Hawkins

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500558

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      The [4+2] cycloaddition reaction of low aromatic 3,4,5-triphenyl-1-(+)-neomenthyl-1,2-diphosphole with maleic anhydride proceeds under mild conditions with high diastereoselectivity (up to 88 % de) and results in the corresponding enantiopure 1,7-diphosphanorbornene.

  9. Full Papers

    1. Sugar Amino Acids

      Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly

      Vitālijs Rjabovs, Pāvels Ostrovskis, Daniels Posevins, Gļebs Kiseļovs, Viktors Kumpiņš, Anatoly Mishnev and Māris Turks

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500695

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      Syntheses of new γ- and δ-furanoid sugar amino acids have been accomplished. The obtained N-protected building blocks are suitable for chain elongation, as was verified by the synthesis of tetrameric carbopeptoids.

    2. Chalcogen-Nitrogen Heterocycles

      [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selena­diazole and Generation of Persistent Radical Anions

      Lidia S. Konstantinova, Irina E. Bobkova, Yulia V. Nelyubina, Elena A. Chulanova, Irina G. Irtegova, Nadezhda V. Vasilieva, Paula S. Camacho, Sharon E. Ashbrook, Guoxiong Hua, Alexandra M. Z. Slawin, J. Derek Woollins, Andrey V. Zibarev and Oleg A. Rakitin

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500742

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      3,4-Diamino-1,2,5-selenadiazole was synthesized and used for preparing novel [1,2,5]selenadiazolo[3,4-b]pyrazines. Electrochemical reduction of the latter into persistent radical anions (RAs) was studied by CV and the RAs were characterized by EPR combined with DFT calculations.

  10. Short Communications

    1. Allylic Alkynylation

      Pd-Catalyzed Allylic Alkynylation of Allylic Acetates with Terminal Alkynes

      Qingjing Yang, Yongyun Zhou, Jingchao Chen, Xiaobo He, Jianbin Xu, Fuk Yee Kwong and Baomin Fan

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500522

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      Allylic alkynylation of allylic acetates with terminal aryl alkynes was developed by using a palladium/silver co-catalyst. In the presence of Pd(OAc)2 and AgOTf combined with 1,1′-bis(diphenylphosphino)ferrocene (DPPF), various 1,4-enynes were obtained in moderate to excellent yields in toluene at 50 °C, which offers a new and efficient method for the construction of functionalized 1,4-enyne skeletons.

  11. Full Papers

    1. Transesterification

      Enzymatic Synergism in the Synthesis of β-Keto Esters

      Catalina Wiśniewska, Dominik Koszelewski, Małgorzata Zysk, Szymon Kłossowski, Anna Żądło, Anna Brodzka and Ryszard Ostaszewski

      Article first published online: 22 JUL 2015 | DOI: 10.1002/ejoc.201500676

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      Application of a selected enzyme mixture for enzyme-catalyzed esterification of various carboxylic acids provided the respective β-hydroxy esters in excellent yields up to 96 % and quantitative within 24 and 48 hours, respectively.

    2. Asymmetric Catalysis

      Chiral Squaramide-Catalyzed Michael/­Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes

      Bo-Liang Zhao and Da-Ming Du

      Article first published online: 22 JUL 2015 | DOI: 10.1002/ejoc.201500533

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      A cascade cyclopropanation reaction between (E)-3-arylenechroman-4-one or (E)-2-arylideneindan-1-one derivatives and a bromonitroalkane with a chiral squaramide catalyst has been developed. Nitro-spirocyclopropanes were obtained in moderate to good yields (up to 90 %) with enantioselectivities up to >99 % ee (enantiomeric excess) and diastereoselectivities up to >99:1 dr (diastereomeric ratio).

    3. Carbocation Rearrangements

      Isomerization of the 2-Norbornyl Carbocation

      Kevin A. Lobb

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500518

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      There are numerous classical and non-classical isomers of C7H11+, and the transformations connecting these have been mapped revealing multiple redundant pathways for the transformation of the 2-norbornyl carbocation into its most stable isomer, the 1,3-dimethylcyclopentenyl cation.

    4. Reductive Alkylations

      Cobalt-Catalyzed Reductive Alkylation of Heteroaryl Bromides: One-Pot Access to Alkylthiophenes, -furans, -selenophenes, and -pyrroles

      Deng-Jhou Cai, Po-Han Lin and Ching-Yuan Liu

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500784

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      Various alkyl chains have been introduced into organic, electronically important heteroaryl compounds step-economically through Co-catalyzed reductive alkylation reactions. The resulting alkylheteroarenes are indispensable building blocks for polymer chemistry and π-functional organic materials.

  12. Short Communications

    1. Switchable Foldamers

      Conformational Switching in Heterochiral α,β2,3-Hybrid Peptides in Response to Solvent Polarity

      Dhayalan Balamurugan and Kannoth M. Muraleedharan

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500534

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      α,β-Hybrid peptides with a heterochiral backbone show the ability to exist in a helical, extended, or partially folded conformation depending on the solvation conditions employed.

  13. Full Papers

    1. Prins Cyclization

      Domino Prins Cyclization of Enynols: Stereoselective Synthesis of Bicyclic Vinyl Fluorides

      Anipireddy Venkateswarlu, Marumudi. Kanakaraju, Ajit C. Kunwar, Yellala V. Rami Reddy and Basi V. S. Reddy

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500689

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      A fluoride-induced termination of the Prins cyclization observed with a tethered alkyne in the presence of AgSbF6 affords a novel series of 6-fluoro-1-aryl-hexahydro-1H-isochromene derivatives.

    2. Gold Nanoparticle Template

      Water-Soluble Maleimide-Modified Gold Nanoparticles (AuNPs) as a Platform for Cycloaddition Reactions

      Sara Ghiassian, Pierangelo Gobbo and Mark S. Workentin

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500685

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      The scope of reactivity of small water-soluble maleimide-modified gold nanoparticles is expanded to include Diels–Alder and 1,3-dipolar nitrone cycloaddition reactions.

    3. Tandem Dehydration–Oxidation

      Copper/Selectfluor-System-Catalyzed Dehydration–Oxidation of Tertiary Cyclo­alcohols: Access to β-Substituted Cyclohex-2-enones, 4-Arylcoumarins, and Bi­aryls

      Shaobo Ren, Jian Zhang, Jiahui Zhang, Heng Wang, Wei Zhang, Yunkui Liu and Miaochang Liu

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500610

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      A route to β-substituted cyclohex-2-enones, 4-arylcoumarins, and biaryls has been developed. This approach involves a one-pot Cu0/Selectfluor-catalyzed dehydration–oxidation of tertiary cycloalcohols.

    4. Donor–Acceptor Systems

      T-Shaped (Donor–π–)2Acceptor–π–Donor Push–Pull Systems Based on Indan-1,3-dione

      Parmeshwar Solanke, Filip Bureš, Oldřich Pytela, Milan Klikar, Tomáš Mikysek, Loic Mager, Alberto Barsella and Zdeňka Růžičková

      Article first published online: 20 JUL 2015 | DOI: 10.1002/ejoc.201500525

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      T-shaped chromophores based on an indan-1,3-dione central acceptor with systematically varied peripheral donors are investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectroscopy, differential scanning calorimetry (DSC), electric-field-induced second-harmonic generation (EFISHG) studies, and DFT calculations. Structure–property relationships are subsequently elucidated.

  14. Short Communications

    1. C–H Functionalization

      Undecorated Cu(OAc)2-Catalyzed C(sp3)–C(sp3) Bond Formation through para-Hydroxy Group Triggered Remote Benzylic C(sp3)–H Bond Functionalization

      Jian-Gang Huang, Ying Guo, Yu-Dan Li, Hong-Wei Liu, Dao-Hua Liao and Ya-Fei Ji

      Article first published online: 17 JUL 2015 | DOI: 10.1002/ejoc.201500706

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      The Cu(OAc)2-catalyzed para-hydroxy group triggered oxidative coupling of 2,6-disubstituted-4-cresols with fluorinated β-ketone esters or malonates leading to benzylic C(sp3)–C(sp3) bond formation is described with ambient air as the terminal oxidant. Highly functionalized 3-phenylpropanoate derivatives containing fluorinated quaternary carbon-like centers are constructed in an ecofriendly manner.

  15. Full Papers

    1. β-Amino Acid Synthesis

      A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters

      Fan Xu, Qiongsi Wu, Xiaoyang Chen, Xianfu Lin and Qi Wu

      Article first published online: 17 JUL 2015 | DOI: 10.1002/ejoc.201500760

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      A one-pot protocol for simultaneous synthesis of chiral β-amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL-B) catalysed aza-Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β-amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.

    2. Acylation of Nucleobases

      Ferrocenoyl-Substituted Pyrimidine Nucleobases: An Experimental and Computational Study of Regioselective Acylation of Uracil, Thymine, and 5-Fluorouracil

      Jasmina Lapić, Valentina Havaić, Davor Šakić, Krešimir Sanković, Senka Djaković and Valerije Vrček

      Article first published online: 17 JUL 2015 | DOI: 10.1002/ejoc.201500647

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      NMR spectroscopy and quantum chemical calculations (DFT) were employed to rationalize the regioselectivity in the formation of ferrocenoyl-substituted pyrimidine nucleobases. A facile one-step method is reported for the synthesis of N1-substituted derivatives.

    3. 2H-Chromenes

      Construction of Diverse and Functionalized 2H-Chromenes by Organocatalytic Multicomponent Reactions

      Hongyun Cai, Likai Xia, Yong Rok Lee, Jae-Jin Shim and Sung Hong Kim

      Article first published online: 17 JUL 2015 | DOI: 10.1002/ejoc.201500616

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      A green method for the regioselective synthesis of highly functionalized 2H-chromenes has been developed by using L-proline-catalyzed multicomponent reactions of salicylaldehydes, electron-deficient alkynes, and alcohols. Some quinolines and coumarins were synthesized as an extension of this approach, and a possible reaction mechanism is also presented.

    4. Heterocyclic Chemistry

      Methodology for Synthesis of Enantiopure 3,5-Disubstituted Pyrrol-2-ones

      Ondřej Krenk, Jiří Kratochvíl, Marcel Špulák, Vladimír Buchta, Jiří Kuneš, Lucie Nováková, Mukund Ghavre and Milan Pour

      Article first published online: 17 JUL 2015 | DOI: 10.1002/ejoc.201500620

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      A new method has been developed for the synthesis of 3,5-disubstituted pyrrol-2-ones. This protocol allows for the preparation of a large number of compounds by choosing different precursors at a late stage in the synthesis. The antimicrobial activity for some of the synthesized compounds was also examined.

    5. Natural Product Synthesis

      A Non-Aldol Preparation of Enantiopure Propionate-Derived Motifs with the Assistance of Chiral Sulfoxides: Application to a Convergent Synthesis of the Lactone Core of Octalactins

      Claude Bauder

      Article first published online: 17 JUL 2015 | DOI: 10.1002/ejoc.201500527

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      The synthesis of enantiopure propionate-derived motifs by a non-aldol process was achieved by using a chiral sulfoxide. The products were applied in the preparation of a medium-ring lactone.

    6. α-Oxo-Iminoxyls

      α-Oxo-Iminoxyls of Isoxazolones, Pyrazol­ones and 1,2,3-Triazolone

      Rainer Koch, Hans-Joachim Wollweber, Hans Müller-Starke and Curt Wentrup

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500728

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      α-Oxo-iminoxyls derived from 4-oximinoisoxazol-5(4H)-ones, 4-oximinopyrazol-5(4H)-ones, and 1-phenyl-4-oximino-1,2,3-triazol-5(4H)-one have been characterized by electron spin resonance spectroscopy in conjunction with DFT calculations of structures, energies, and hyperfine coupling constants. The outcome is a clear-cut assignment of Z and E structures of the radicals in solution.

    7. Heterocyclic Chemistry

      Synthesis of Pyrimidine-Fused Benzazepines from 5-Allyl-4,6-dichloropyrimidines

      Lina M. Acosta-Quintero, Jorge Jurado, Manuel Nogueras, Alirio Palma and Justo Cobo

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500632

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      An efficient two-step protocol to access a new series of polysubstituted 6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepines from readily available 5-allyl-4,6-dichloropyrimidines is described for the first time.

    8. Lewis Acid Catalyzed Cyclization

      Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydro­benzo[e]azulenes

      Donald B. Konopacki, Kelley C. Shortsleeves, Mark M. Turnbull, Jan L. Wikaira and Adrian D. Hobson

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500452

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      The Lewis acid catalyzed Baylis–Hillman reaction has been used for the stereoselective synthesis of fused 5–7–6 ring systems. The isolation of an unexpected regioisomer from the reaction with (methylphenyl)propionaldehyde provides insights into the probable mechanisms operative in the reaction.

    9. Fluorescent Organoboron Complexes

      Synthesis and Optical Properties of a Series of Green-Light-Emitting 2-(4-Phenylquinolin-2-yl)phenol–BF2 Complexes (Boroquinols)

      Umamahesh Balijapalli and Sathiyanarayanan Kulathu Iyer

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500461

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      2-(4-Phenylquinolin-2-yl)phenol derivatives were complexed with boron trifluoride to give four-coordinate fluorescent organoboron complexes (em = 470–560 nm). The complexes exhibited luminescence in both solution and solid states, with large Stokes shifts (3688–10231 cm–1). Emission in the green region with quantum yields up to 22 % in CHCl3 was observed.

    10. Supramolecular Catalysis

      A Double-Cavity-Containing Porphyrin Host as a Highly Stable Epoxidation Catalyst

      Paul J. Thomassen, Shaji Varghese, Edward J. A. Bijsterveld, Pall Thordarson, Johannes A. A. W. Elemans, Alan E. Rowan and Roeland J. M. Nolte

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500492

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      A highly stable double-cavity-containing catalytic porphyrin host has been developed. A pyridine ligand bound in one of the cavities regulates the rate and selectivity of an epoxidation reaction that takes place in the other cavity. Binding studies suggest that site-to-site communication exists between the two cavities.

  16. Microreviews

    1. Enantiopure Nitrogen Heterocycles

      Substrate Activation in the Catalytic Asymmetric Hydrogenation of N-Heteroarenes

      Bugga Balakrishna, José Luis Núñez-Rico and Anton Vidal-Ferran

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500588

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      This microreview highlights progress in synthetically manipulating heteroaromatic compounds in order to increase their reactivity towards asymmetric hydrogenation mediated by enantiomerically pure transition-metal complexes.

  17. Short Communications

    1. Organoselenium Chemistry

      Synthesis of 3-Selenylindoles under Eco­friendly Conditions

      Natasha L. Ferreira, Juliano B. Azeredo, Breno L. Fiorentin and Antonio L. Braga

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500514

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      The synthesis of biologically relevant 3-selenylindoles by using a catalytic amount of K2CO3 and ethanol as an ecofriendly reaction medium in a system open to air is described. Through this approach, a series of 3-selenylindoles are obtained in good yields by a radical pathway.

    2. C–H Oxidation

      Selectfluor–Bu4NI-Mediated C(sp3)–H Oxidation in Aqueous Media: Synthesis of Δ2-Isoxazolines from Oximes

      Di Shi, Hai-Tao Qin, Chen Zhu and Feng Liu

      Article first published online: 15 JUL 2015 | DOI: 10.1002/ejoc.201500780

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      The title reaction involves Selectfluor–Bu4NI-mediated C–O bond formation in aqueous media under metal-free conditions. A variety of Δ2-isoxazolines are directly synthesized from oximes by remote intramolecular functionalization of C(sp3)–H bonds.

  18. Full Papers

    1. Total Synthesis

      An Efficient Stereoselective Total Synthesis of All Stereoisomers of the Antibiotic Thiamphenicol through Ruthenium-Catalyzed Asymmetric Reduction by Dynamic Kinetic Resolution

      Marc Perez, Pierre-Georges Echeverria, Elsa Martinez-Arripe, Mehdi Ez Zoubir, Ridha Touati, Zhaoguo Zhang, Jean-Pierre Genet, Phannarath Phansavath, Tahar Ayad and Virginie Ratovelomanana-Vidal

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500661

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      An expedient synthesis for the four isomers of the broad-spectrum antibiotic thiamphenicol is described through either a ruthenium-catalyzed asymmetric hydrogenation or a transfer hydrogenation reaction by a dynamic kinetic resolution.

    2. Synthetic Methodology

      Synthesis of 3-(Trifluoromethyl)pyrazoles and Polysubstituted Pyrazoles by a tBuOK-Mediated Intramolecular Cycli­zation

      Jia-Jie Wen, Cheng-Ke Ding, Zong-Cang Ding, Ting Li and Zhuang-Ping Zhan

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500705

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      A highly efficient tBuOK-mediated synthesis of 3-(trifluoromethyl)pyrazoles and other polysubstituted pyrazoles by intramolecular cyclization of N-propargylhydrazones with excellent yields is reported.

    3. Self-Assembly

      Synthesis and NMR Spectroscopic Study of the Self-Aggregation of 2-Substituted Benz­ene-1,3,5-tricarboxamides

      Christian Invernizzi, Claudio Dalvit, Helen Stoeckli-Evans and Reinhard Neier

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500506

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      The columnar self-assembly of a new class of 2-substituted N,N′,N″-trialkylbenzene-1,3,5-tricarboxamides is reported. Hydrogen-bond-accepting substituents (e.g., alkoxy and alkynyloxy) were demonstrated to impair the columnar self-assembly process, whereas non-hydrogen-bond-accepting groups (e.g., bromine) strengthened the self-assembly process.

  19. Short Communications

    1. Corrole-Porphyrin Dendrimers

      Corrole-Decorated Porphyrin Dendrimer and Its Selective Metallation

      Nikolay Semenishyn, Atif Mahammed and Zeev Gross

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500752

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      The center and the branches of the corrole-decorated porphyrin dendrimer may be selectively metallated.

    2. Efficient Perylenebisimide Synthesis

      Fast and Efficient Microwave-Assisted Synthesis of Perylenebisimides

      Francesco Rigodanza, Eleonora Tenori, Aurelio Bonasera, Zois Syrgiannis and Maurizio Prato

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500670

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      Perylenebisimides (PBIs) are dyes which can be used in a wide variety of applications. Much effort has been devoted on the synthesis of these materials. Herein, we present the successful synthesis of different PBIs derivatives with the use of microwave irradiation. The products are collected in very good yields, in short time and with high purity.

    3. Organocatalysis

      Tertiary Amine Promoted Asymmetric ­Aldol Reaction of Aldehydes

      Bartosz Gut and Jacek Mlynarski

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500519

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      The direct asymmetric self-aldol reactions of various α-oxyaldehydes catalyzed by tertiary amines have been demonstrated. By using 10 mol-% of quinine catalyst, dimerization products have been formed in high yields, with good anti-diastereocontrol, and up to 80 % ee.

  20. Full Papers

    1. Vinyl Addition

      Regioselective Synthesis of 6-Vinyl-3,6-dihydropyridine-2(1H)-ones through Simple Addition of a Vinylmagnesium “Ate” Complex to 2-Pyridones

      Jacek G. Sośnicki, Przemysław Dzitkowski and Łukasz Struk

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500605

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      The vinyl “ate” complex (lithium vinyldimethylmagnesate) formed directly by mixing vinylMgCl and MeLi is, unlike a simple Grignard reagent, nucleophilic enough that it undergoes addition to N-substituted 2-pyridones.

    2. Natural Product Synthesis

      Divergent and Concise Syntheses of Spiroisoxazolines: First Total Synthesis of 11-Deoxyfistularin-3

      Prasanta Das and Ashton T. Hamme II

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500603

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      A complementary route for spiroisoxazolines leads to the total synthesis of 11-deoxyfistularin-3.

    3. Energetic 1,3,4-Oxadiazoles

      Synthesis, Characterization and Energetic Properties of 1,3,4-Oxadiazoles

      Zuoquan Wang, Hong Zhang, Benjamin J. Killian, Farukh Jabeen, Girinath G. Pillai, Heather M. Berman, Michael Mathelier, Ashani J. Sibble, Justin Yeung, Wenfeng Zhou, Peter J. Steel, C. Dennis Hall and Alan R. Katritzky

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejoc.201500583

      Thumbnail image of graphical abstract

      Efficient cyclization between nitro-substituted benzohydrazides and nitro-substituted benzoic acids affords energetic 1,3,4-oxadiazoles.

    4. Enantioselective Synthesis

      An Enantioselective Synthesis of Substituted Cyclohexanone Derivatives with an All-Carbon Quaternary Stereocenter by Using an Organocatalytic Asymmetric Domino Double Michael Addition

      Chi-Han Chen, Chi-Ting Ko, Ganapuram Madhusudhan Reddy, Chia-Jui Lee and Wenwei Lin

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500524

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      A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.

  21. Short Communications

    1. Synthetic Methods

      Chemoselective Synthesis of 5-Alkylamino-1H-pyrazole-4-carbaldehydes by Cesium- and Copper-Mediated Amination

      Jessica Orrego-Hernández, Justo Cobo and Jaime Portilla

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500505

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      Hereby is described an efficient protocol for the chemoselective synthesis of new 5-alkylaminopyrazole-4-carbaldehydes from 5-chloropyrazole-4-carbaldehydes and primary alkylamines in one step to give products with good to excellent yields and short reaction times. Unexpectedly, under these reaction conditions the corresponding alkylimine formation was not observed.

  22. Full Papers

    1. Borazaroquinolines

      Synthesis of 2,1-Borazaroquinolines and 2,1-Borazaroisoquinolines from Vinyl­aminopyridines and Potassium Organotrifluoroborates by Microwave-Assisted Heating

      M. Rosa Sánchez Casado, Myriam Ciordia Jiménez, Manuela Ariza Bueno, Morgane Barriol, Joseph E. Leenaerts, Chiara Pagliuca, Carolina Martínez Lamenca, Ana Isabel De Lucas, Aránzazu García, Andrés A. Trabanco and Frederik J. R. Rombouts

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500622

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      A diversely substituted set of new 2,1-borazaroquinolines and 2,1-borazaroisoquinolines has been synthetized from (vinylamino)pyridines and potassium organotrifluoroborates using microwave heating.

    2. Glycolipid Syntheis

      First Total Synthesis of Ganglioside GAA-7 from Starfish Asterias amurensis versi­color

      Hideki Tamai, Akihiro Imamura, Junya Ogawa, Hiromune Ando, Hideharu Ishida and Makoto Kiso

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500606

      Thumbnail image of graphical abstract

      The first total synthesis of neuritogenic ganglioside GAA-7 was achieved using the glucosyl ceramide cassette approach. The neuritogenic activities of the synthesized GAA-7 and its glycan moiety were also examined.

    3. Cross-Coupling

      Synthesis of Diverse 6-Oxa-allocolchicinoids by a Suzuki–Miyaura Coupling, Acid-Catalyzed Intramolecular Transacetali­zation Strategy

      Dharmendra B. Yadav, Lebusetsa Taleli, Alet E. van der Westhuyzen, Manuel A. Fernandes, Maxim Dragoun, Aram Prokop, Hans-Günther Schmalz, Charles B. de Koning and Willem A. L. van Otterlo

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500573

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      28 novel substituted 6-oxa-allocolchicinoids (5-alkoxy-5,7-dihydrodibenzo[c,e]oxepines) were synthesized by way of a Suzuki–Miyaura coupling reaction, followed by an acid-catalyzed intramolecular transacetalization with different alcohols. One of the compounds was shown to sensitize vincristine-resistant leukemia and lymphoma cells to vincristine.

    4. Modular Luminophore Synthesis

      Two-Step Synthesis of Blue Luminescent (Pyrrol-3-yl)-1H-(aza)indazoles Based on a Three-Component Coupling–Cyclocondensation Sequence

      Jan Nordmann, Svenja Eierhoff, Melanie Denißen, Bernhard Mayer and Thomas J. J. Müller

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500575

      Thumbnail image of graphical abstract

      A consecutive three-component synthesis for ortho-halo-3-acylpyrrol-3-yl-substituted (hetero)arenes followed by a cyclization–condensation–SNAr sequence opens an efficient modular approach to blue luminescent (pyrrol-3-yl)-1H-(aza)indazoles.

  23. Microreviews

    1. 4′-Selenonucleosides

      4′-Selenonucleosides as Next-Generation Nucleosides

      Pramod K. Sahu, Siddhi D. Naik, Jinha Yu and Lak Shin Jeong

      Article first published online: 8 JUL 2015 | DOI: 10.1002/ejoc.201500429

      Thumbnail image of graphical abstract

      Modified nucleosides have served as valuable resources for therapeutic agents such as antiviral and antitumor agents. Because of several adverse effects of old-generation nucleosides, emergence of a new template of modified nucleosides is highly desirable. This review describes the stereoselective synthesis, conformation analysis, and biological activity of various modified 4′-selenonucleosides.

  24. Full Papers

    1. Anion Transport

      Acyclic Pseudopeptidic Hosts as Molecular Receptors and Transporters for Anions

      Inés Martí, M. Isabel Burguete, Philip A. Gale and Santiago V. Luis

      Article first published online: 3 JUL 2015 | DOI: 10.1002/ejoc.201500390

      Thumbnail image of graphical abstract

      Pseudopeptidic structures offer access to the design of efficient anion transmembrane carriers.

    2. Fluorinated Compounds

      A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one

      Denis N. Bazhin, Yulia S. Kudyakova, Gerd-Volker Röschenthaler, Yanina V. Burgart, Pavel A. Slepukhin, Maksim L. Isenov, Victor I. Saloutin and Valery N. Charushin

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500737

      Thumbnail image of graphical abstract

      Reactions of the 2-methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one with N-binucleophiles are useful for the convenient preparation of trifluoromethyl-containing pyrazoles, pyrazolines, quinoxalines, isoxazoles, 1H-furo[2,3-d]imidazol-2(3H)-ones.

    3. Natural Product Synthesis

      Synthesis of the C-8–C-24 Fragment of Maltepolide C by Using a Tandem Di­hydroxylation/SN2 Cyclization Sequence

      Debendra K. Mohapatra, D. Sai Reddy, G. Sudhakar Reddy and Jhillu S. Yadav

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500629

      Thumbnail image of graphical abstract

      A highly stereoselective synthesis of the C-8–C-24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN2 cyclization reaction sequence as the key step.

    4. Polyaromatics

      Synthesis of Annulated Anthracenes, Carb­azoles, and Thiophenes Involving Bradsher-Type Cyclodehydration or Cycli­zation–Reductive-Dehydration Reactions

      Settu Muhamad Rafiq, Ramakrishnan Sivasakthikumaran, Jayachandran Karunakaran and Arasambattu K. Mohanakrishnan

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500493

      Thumbnail image of graphical abstract

      A conventional BF3·OEt2-mediated Bradsher-type cyclodehydration of 2-aryl/heteroaryl methyl benzaldehydes in CH2Cl2 at r.t. gave annulated arenes and heteroarenes in good yields. Alternatively, these anthracene analogues could be synthesized in better yields from the corresponding 2-aryl/heteroarylmethyl benzoic acids by Brønsted-acid-mediated cyclization followed by reductive dehydation.

    5. Glyconanodiamonds

      Thiourea-Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

      Claudia Fessele, Stefan Wachtler, Vijayanand Chandrasekaran, Carina Stiller, Thisbe K. Lindhorst and Anke Krueger

      Article first published online: 29 JUN 2015 | DOI: 10.1002/ejoc.201500532

      Thumbnail image of graphical abstract

      Thiourea-bridging is a new approach to conjugating nanodiamond nanoparticles and biomolecules. This was exemplified by preparation of saccharide-functionalized nanodiamonds (NDs) that were characterized and employed in biological studies. These studies revealed specific ND binding to E. coli bacterial cells.

  25. Short Communications

    1. Peptide Catalysis

      Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane

      Kengo Akagawa, Nobuhiro Nishi, Isao Yoshikawa and Kazuaki Kudo

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500594

      Thumbnail image of graphical abstract

      A kinetic resolution of a planar-chiral [2.2]paracyclophane was attained through the Michael addition of nitromethane in the presence of a resin-supported peptide catalyst. A helical peptide with an appropriate N-terminal sequence was effective for a selective resolution.

  26. Microreviews

    1. Organometallic Rearrangements

      Formal Dyotropic Rearrangements in Organometallic Transformations

      Michael F. Croisant, Ryan Van Hoveln and Jennifer M. Schomaker

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500561

      Thumbnail image of graphical abstract

      Organometallic dyotropic rearrangements involve interchange of two groups on a stationary scaffold by breaking and reforming of two σ bonds. They proceed through various different mechanisms and yield a diverse array of products. This microreview traces recent developments and applications of formal dyotropic rearrangements involving both stoichiometric and catalytic amounts of transition metals.

    2. Hydrogen-Transfer Reactions

      Pd-Catalyzed Hydrogen-Transfer Reactions from Alcohols to C=C, C=O, and C=N Bonds

      Jacques Muzart

      Article first published online: 12 JUN 2015 | DOI: 10.1002/ejoc.201500401

      Thumbnail image of graphical abstract

      Highlights and mechanisms of Pd-catalyzed abstracting and borrowing hydrogen transfers from alcohols are presented.

    3. Unique Lewis Acid Catalysis

      Hafnium Trifluoromethanesulfonate [Hf(OTf)4] as a Unique Lewis Acid in Organic Synthesis

      Haruro Ishitani, Hirotsugu Suzuki, Yuki Saito, Yasuhiro Yamashita and Shū Kobayashi

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500423

      Thumbnail image of graphical abstract

      This microreview summarizes examples of Hf(OTf)4-mediated or -catalyzed organic reactions. Hafnium triflate shows outstanding performance in catalytic Friedel–Crafts acylation reactions and in Mannich-type reactions of imines, hydrazones, and N,O-acetals.

    4. Organocatalysis

      Trifunctional Organocatalysts: Catalytic Proficiency by Cooperative Activation

      Ryan Kenny and Fei Liu

      Article first published online: 28 MAY 2015 | DOI: 10.1002/ejoc.201500179

      Thumbnail image of graphical abstract

      Proficient trifunctional organocatalysts employ an expansive collection of chemical motifs in multiple modes of activation to provide concurrent enhancement in rate and enantioselectivity in complex reactions. These systems demonstrate catalytic cooperativity for a range of C–C, C–N, C–O, and C–X bond-forming reactions.

    5. Niobium Complex Chemistry

      Niobium Complexes in Organic Transformations: From Stoichiometric Reactions to Catalytic [2+2+2] Cycloaddition Reactions

      Yasushi Satoh and Yasushi Obora

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500358

      Thumbnail image of graphical abstract

      Niobium can exist in a number of different oxidation states (from +5 to –3), and it is anticipated that Nb complexes should possess unique reactivity in organic transformations. Previously, low-valent niobium complexes were used as reagents in organic reactions. In recent decades they have been used as catalysts in various [2+2+2] cycloadditions.


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